Manufacture of a follicle hormone-quinoline addition product



Patented July 14, 1936 UNITED STATES PATENT OFFICE MANUFACTURE OF AFOLLICLE HORMONE- QUINOLINE ADDITION PRODUCT Adolf Butenandt, Gottingen,Germany, assignor to Schering-Kahlbaum A. G., Berlin, Germany 3 Claims.

My invention relates to the class of substances known as germinal glandhormones, which includes the follicle hormones, and has for one of itsobjects to provide means for producing combinations of said folliclehormones with other chemical compounds, these combinations being readilysplit up into their constituents, thereby enabling the hormoneconstituent to be obtained in pure state.

I have found that the follicle hormones can easily be made to combinewith quinoline, compounds insoluble in water being obtained which formfine crystals. These compounds can be made use of with particularadvantage for the purification of the follicle hormones, since on beingacted upon with a dilute acid such as hydrochloric acid or sulphuricacid they will be split up again under the formation of the unchangedhormones. I have found this method to be particularly suitable in theseparation of the follicle hormones from partly purified, however notaltogether pure hormone preparations.

In practicing my invention I may for instance proceed as follows:-

Example 1 part of the crude follicle hormone Ciel-12202 is mixed with anequal quantity, by weight, of quinoline and the mixture cautiouslyheated so as to obtain complete solution. When this solution cools down,it solidifies as a whole, forming a crystal broth which is freed from'liquid by pressing it onto a piece of unglazed pottery. The

departing from the invention or sacrificing the 15 advantages thereof.

I claim:

1. The molecular addition compounds of the follicle hormones withquinoline, being well crystallized substances insoluble in'water.

2. The molecular addition compound of the follicle hormone C18H2202 withquinoline, having the formula C1aH2202C9H7N, melting at 210 C. and beingrecrystallizable from its solutions in ether and in pure alcohol andreadily decomposed into its components in dilute alcohol.

3. The method of producing the addition compound of claim 1, comprisingcautiously heating equal parts by weight of the two reagents to obtaincomplete solution, allowing the solution to cool down and freeing thecrystal broth, which is thereby formed, from the liquid adhering to it.

ADOLF BUTENANDT.

